As an Undergraduate Bill Earned All-American honors in 1991, 92 & 93. After graduating St. Mary’s College of Maryland, Bill became the Varsity Dinghy Coach for the US Coast Guard Academy from 1996-2000. Healy also coached numerous US Youth Championships and a Youth World Championship. After a short stint outside the coaching world, Bill became the Assistant sailing coach for the Bulldogs in 2003. Since then the Elis have won eight National Championships. Healy is also an accomplished sailor. Having won just about every major U.S. International 420 regatta, Healy is a perfect match for the fleet of Yale 420's. In 1994 Healy was a member of the US Sailing 470 Team and is National, North American or Mid-Winter champions in 5 different sailing classes.

In 2017, Healy was awarded the Sail1Design Coach of the Year Award for being the best one design dinghy coach. He was given nine lengthy and heartfelt nominations from sailors he has coached over the years.